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Interguanine hydrogen-bonding patterns in adducts with water and Zn–purine complexes (purine is 9-methyladenine and 9-methylguanine). Unexpected preference of Zn(II) for adenine-N7 over guanine-N7

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Abstract

Guanine–guanine hydrogen bonding involving the Watson–Crick edge [N(1)H, N(2)H2] of one base and the Hoogsteen edge (N7, O6) of the other is the dominant association pattern in the solid-state structures of two hydrates of 9-ethylguanine (9-EtGH), and in adducts of 9-methylguanine (9-MeGH) with the Zn compounds [ZnCl2(H2O)(9-MeGH-N7)]·(9-MeGH) as well as [ZnCl2(H2O)(9-MeA-N7)]·2(9-MeGH) (9-MeA is 9-methyladenine). The structures of 9-EtGH·2H2O and 9-EtGH·3.5H2O are dominated by polymeric tape structures of the guanine and extended water clusters. In [ZnCl2(H2O)(9-MeGH-N7)]·(9-MeGH) the metalated guanine is involved in hydrogen bonding (GG3 motif) with a free 9-MeGH, which in turn is centrosymmetrically related to itself via hydrogen bonds involving N(2)H2 and N3 (GG4 motif). In [ZnCl2(H2O)(9-MeA-N7)]·2(9-MeGH) the metalated adenine base interacts via its Watson–Crick edge [N1, N(6)H2] with the sugar edge [N(2)H2, N3] of one of the guanine nucleobases of the GG pair. Crystallization of [ZnCl2(H2O)(9-MeA-N7)]·2(9-MeGH) from an aqueous solution containing 9-MeGH, 9-MeA, and ZnCl2 is fully unexpected in that the anticipated preference of Zn(II) for guanine-N7 is not realized and instead coordination to adenine-N7 is observed. The relevance of [ZnCl2(H2O)(9-MeGH-N7)]·(9-MeGH) and [ZnCl2(H2O)(9-MeA-N7)]·2(9-MeGH) for metal-containing nucleic acid triplex structures is discussed.

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Acknowledgements

This work was supported by the Deutsche Forschungsgemeinschaft (DFG) and the Spanish Ministerio de Educación y Ciencia (NAN2004-09183-C10-06 and MAT2004-05589-C02-02).

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Authors and Affiliations

  1. Departamento de Tecnología Industrial, Universidad Alfonso X “El Sabio”, 28691 Villanueva de la Cañada, Madrid, Spain

    Pilar Amo-Ochoa

  2. Departamento de Química Inorgánica, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080, Bilbao, Spain

    Oscar Castillo

  3. Fachbereich Chemie, Universität Dortmund, Otto-Hahn-Strasse 6, 44221, Dortmund, Germany

    Pablo J. Sanz Miguel & Bernhard Lippert

  4. Departamento de Química Inorgánica, Universidad Autónoma de Madrid, 28049, Madrid, Spain

    Pablo J. Sanz Miguel & Félix Zamora

  5. Department of Chemistry, University of Virginia, McCormick Road, Charlottesville, VA, 22901, USA

    Michal Sabat

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  1. Pilar Amo-Ochoa
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  2. Pablo J. Sanz Miguel
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  4. Michal Sabat
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Correspondence to Bernhard Lippert or Félix Zamora.

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Amo-Ochoa, P., Sanz Miguel, P.J., Castillo, O. et al. Interguanine hydrogen-bonding patterns in adducts with water and Zn–purine complexes (purine is 9-methyladenine and 9-methylguanine). Unexpected preference of Zn(II) for adenine-N7 over guanine-N7. J Biol Inorg Chem 12, 543–555 (2007). https://doi.org/10.1007/s00775-007-0206-1

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